Sodium Bicarbonate → tert-butyl (1-(4-(9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-2-yl)phenyl)cyclobutyl)carbamate

HRID 1046987Notes

Reaction equation

HRID 1046987 reaction equation
O=[C:2]1[N:8]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=O)[C:7]2[CH:30]=[CH:31][CH:32]=[N:33][C:6]=2[NH:5][C:4]2[CH:34]=[CH:35][CH:36]=[CH:37][C:3]1=2.C([O-])(=O)C.[NH4+:42].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[N:42]1[C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:28])[CH3:26])[CH2:19][CH2:20][CH2:21]3)=[CH:16][CH:17]=2)=[CH:9][N:8]2[C:2]=1[C:3]1[CH:37]=[CH:36][CH:35]=[CH:34][C:4]=1[NH:5][C:6]1[N:33]=[CH:32][CH:31]=[CH:30][C:7]2=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 69087642tert-butyl (1-(4-(2-(6-oxo-6,11-dihydro-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-5-yl)acetyl)phenyl)cyclobutyl)carbamate

Product 1

HCID 136331864tert-butyl (1-(4-(9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-2-yl)phenyl)cyclobutyl)carbamateYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of tert-butyl (1-(4-(2-(6-oxo-6,11-dihydro-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-5-yl)acetyl)phenyl)cyclobutyl)carbamate (0.3 g, 1 eq.) in acetic acid (5 mL) was added ammonium acetate (1.5 g, 20 eq.). The reaction was stirred at 120° C. for 2 hours. The reaction was carefully poured onto a saturated sodium bicarbonate solution (10 mL). The mixture was extracted with dichloromethane (3×25 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The product was purified by column chromatography (25-100% ethyl acetate in hexanes), giving tert-butyl (1-(4-(9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-2-yl)phenyl)cyclobutyl)carbamate (0.21 g, 73%). LCMS: 480 [M+H].

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×25 mL)
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by column chromatography (25-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-eadb4bbc72424396a257d3ab496fc706
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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